Robb Report Vices

A History Buff’s Guide to NYC Vices

To celebrate all that is praiseworthy about the United States, one needn’t look much further than the original melting pot—New York City. Sure you can visit Ellis Island and its beacon, the Statue of Liberty, but we’d be hard-pressed to tell you anything about those popular tourist destinations that you don’t already know.

If you’re seeking a unique New York City history lesson, we recommend a stop at any (or all) of the following destinations. After all, these are institutions that our forebears enjoyed, and we can think of no better way to honor their memories than by raising a pint where they themselves once did.

Fraunces Tavern—an all-in-one tavern, restaurant, and museum—has played host to Delancey, van Cortlandt, and more historic names than you’ve likely heard on local subway intercoms. The site dates back to colonial Manhattan, and according to some stories, George Washington lifted his glass in celebration here following his election as president. Oh, and the tavern is a fixture on the American Whiskey Trail, which means thirsty patrons are certain to find a fine selection of brown spirits at the ready.

Like many long-standing brands, the Nat Sherman empire began with one person. According to folklore, Sherman was the quintessential man-about-town, initially operating one of the more lucrative businesses a man living in Prohibition-era New York could own—a speakeasy. It was only much later in his career (after a series of wise investments) that Sherman came to own a premium tobacco business with a storefront on Broadway, one of Manhattan’s busiest avenues. The old Manhattan-elite cigar store and lounge has since relocated to a three-story townhouse on 42nd Street (right off 5th Avenue), but the business and the customer service continue to operate just as they always have.

Since the 1930s, more presidents, dignitaries, Hollywood celebrities, and business tycoons have dined and clinked glasses in the 21 Club than most any other place in the United States. While it’s true that most seats in the restaurant come with some history, we recommend a meal at table 30, affectionately referred to as the “Bogart table” in honor of the legendary actor (it was his favorite spot in the house). The restaurant’s elaborate decorative ceilings are sure to catch your eye, but don’t overlook a PT-109 torpedo-boat model (gifted by President John F. Kennedy), a baseball bat from Willie Mays, a replica of Air Force One from President Clinton, tennis racquets from Chris Evert and John McEnroe, and a golf club once wielded by the Golden Bear, Jack Nicklaus.

Walking into JJ Hatters is like taking a step back in time—a time when men tipped their hats to women on the street and when being a gentleman required a brim. The historic store is considered by many to be New York’s oldest hat store, and upon entering, a prospective customer is met with hundreds of hats and styles. The store is, in many respects, an ode to timeless style. Forget about that guy Pharrell, these guys actually know hats.

Established in 1854, McSorley’s Old Ale House in the East Village is one of the oldest operating saloons in the country. As such, it enforced some odious policies. For example, in 1970 the courts finally ruled that the saloon (one of the country’s last men-only bars) would finally have to open its doors to women. Much has changed about the neighborhood outside of McSorley’s doors, but no matter if you’re a president, a resident, an author, or a thief, the establishment holds firm on one golden rule: “Be good or be gone.”